Water → HCID 52951272, 화합물

HRID 508602노트

반응식

HRID 508602 반응식
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1.C(N(CC)CC)C.O>CN(C=O)C>[C:7]1([C:5]2[N:4]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:20])=[O:21])=[CH:15][CH:14]=3)[N:3]=[C:2]([NH:1][C:32]([NH:31][C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=3)=[O:33])[CH:6]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 52951166HCID 52951166, 화합물

생성물 1

HCID 52951272HCID 52951272, 화합물수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of amine 6 (0.1 g, 0.32 mmol) in 5 mL of DMF was added 3-(trifluoromethyl)phenyl isocyanate (0.12 g, 0.62 mmol) followed by triethylamine (0.05 mL, 0.32 mmol) at 0° C. The reaction mixture was warmed up to room temperature and stirred overnight. The reaction mixture was poured into water, and the resulting precipitates were collected and washed with water. The crude product was purified by column chromatography by dry loading method to give the titled compound (0.13 g, 81% yield). mp 195.1-197.0° C. 1H NMR (300 MHz, DMSO-d6): δ 9.48 (s, 1H), 9.21 (s, 1H), 8.07 (s, 1H), 7.80 (d, J=9 Hz, 2H), 7.61-7.26 (m, 12H), 6.81 (s, 1H). MS (ESI) m/z: 502.12 (M+H+). Anal. Calcd for C23H18F3N5O3S.0.36CH4O: C, 54.69; H, 3.82; N, 13.65. Found: C, 54.69; H, 3.70; N, 13.44.

후처리

  1. customthe resulting precipitates
  2. customwere collected
  3. washwashed with water
  4. customThe crude product was purified by column chromatography
  5. customby dry loading method

출처 및 근거

ORD 기록
ord-5c682b22891e4bd895909b27dd4c393a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096532B2

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